Dimethylformamide → HCID 86652853, compound

HRID 1188975Notes

Reaction equation

HRID 1188975 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][O:9][C:10]2[CH:11]=[C:12]([O:28][C:29]3[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=3)[CH:13]=[C:14]3[C:18]=2[NH:17][C:16]([C:19]2[S:20][CH:21]([CH2:24][C:25](O)=[O:26])[CH2:22][N:23]=2)=[CH:15]3)[CH:5]=[CH:4][CH:3]=1.Cl.C[N:41](C)CCCN=C=NCC.[NH4+].ON1C2C=CC=CC=2N=N1.CN(C)C=O>O>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][O:9][C:10]2[CH:11]=[C:12]([O:28][C:29]3[CH:30]=[CH:31][C:32]([S:35]([CH3:38])(=[O:36])=[O:37])=[CH:33][CH:34]=3)[CH:13]=[C:14]3[C:18]=2[NH:17][C:16]([C:19]2[S:20][CH:21]([CH2:24][C:25]([NH2:41])=[O:26])[CH2:22][N:23]=2)=[CH:15]3)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 86652854HCID 86652854, compound

Product 1

HCID 86652853HCID 86652853, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (2-{7-[(6-chloropyridin-2-yl)methoxy]-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetic acid (180 mg), 1-[3-(dimethylamino)propyl-3-ethylcarbodiimide hydrochloride (161 mg), 1-hydroxybenzotriazole ammonium salt (128 mg) and N,N-dimethylformamide (10 mL) was stirred at room temperature for 15.5 hr. Water was added to the reaction solution, and the precipitated solid was collected by filtration, and washed successively with water, ethanol and diethyl ether. The obtained brown solid was recrystallized from ethanol to give the title compound (115 mg, yield 64%) as colorless crystals. melting point 147-148° C. MS 571 (MH+).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed successively with water, ethanol and diethyl ether
  3. customThe obtained brown solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-8e087fc6049c43f88a177f819759f53f
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

Loading…